57681-53-5Relevant academic research and scientific papers
A facile synthesis of γ-butenolides via cyclization of 3-alkenoic acids with dimethyl sulfoxide and oxalyl bromide
Ding, Rui,Liu, Yongguo,Liu, Lei,Li, Huimin,Tao, Sichen,Sun, Baoguo,Tian, Hongyu
supporting information, p. 3001 - 3007 (2019/08/26)
The combination of dimethyl sulfoxide and oxalyl bromide was used to accomplish the cyclization of 3-alkenoic acids with the aid of a base to afford γ-butenolides, in which bromodimethylsulfonium salt generated in situ was proposed to serve as a Br+ source.
Preparation method of alpha, beta-unsaturated-gamma-lactone
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Paragraph 0005; 0014; 0015, (2018/09/08)
The invention relates to a preparation method of alpha, beta-unsaturated-gamma-lactone shown as a structural formula below. The preparation method comprises the following steps: firstly dropwise adding a dichloromethane solution of dimethylsulfoxide (1.5 equiv) into a dichloromethane solution of oxaloyl bromide (1.5 equiv) at a temperature of 10 DEG C below zero, dropwise adding raw material (E) 3-alkenoic acid, then returning to a room temperature for reaction, adding a potassium carbonate aqueous solution and continuously reacting to obtain the corresponding alpha, beta-unsaturated-gamma-lactone; the yield is 85-90 percent.
Lewis base-catalyzed electrophilic lactonization of selenyl bromide resin and facile solid-phase synthesis of furan-2(5H)-one derivatives
Jun He, Rong,Chun Zhu, Bing,Wang, Yu Guang
, p. 523 - 528 (2014/07/07)
A facile solid-phase synthesis approach was developed for the rapid synthesis of multi-substituted furan-2(5H)-one derivatives libraries. The synthetic strategy included the selenyl bromide resin-induced electrophilic lactonization catalyzed by Lewis base, lithiation, nucleophilic substitution and oxidation-elimination of the selenium resins. The advantages of the new method are good yields, high purity, straightforward operations and high diversity of the products, lack of odor, and good stability of the selenium resins. Copyright
Convenient synthesis of 5-alkylfuran-2(5H)-ones
Ma, Jie,Wang, Si Hong,Yin, Yan Bing
, p. 3026 - 3031 (2011/08/22)
A convenient synthesis of 5-alkylfuran-2(5H)-ones are described starting from 3-nitropropanoate and aldehydes, promoted by neutral alumina, in 35-60% overall yields, via a condensation-lactonization-elimination pathway. Copyright
Pd-catalyzed 5-endo-trig-type cyclization of β,γ-unsaturated carbonyl compounds: An efficient ring closing reaction to give γ-butenolides and 3-pyrrolin-2-ones
Bajracharya, Gan B.,Koranne, Priti S.,Nadaf, Rashid N.,Gabr, Randa Kassem Mohamed,Takenaka, Kazuhiro,Takizawa, Shinobu,Sasai, Hiroaki
supporting information; experimental part, p. 9064 - 9066 (2011/02/16)
The 5-endo-trig-type cyclization has been performed using a Pd-bis(isoxazoline) catalyst. The present cyclization of β,γ- unsaturated carbonyl compounds gave γ-butenolides and 3-pyrrolin-2-ones in good to excellent yields.
Catalytic use of selenium electrophiles in cyclizations
Browne, Danielle M.,Niyomura, Osamu,Wirth, Thomas
, p. 3169 - 3172 (2008/02/10)
A new and convenient one-pot method for a catalytic addition-elimination reaction using selenium electrophiles has been developed. In the presence of 5 mol % diphenyl diselenide, [bis(trifluoroacetoxy)iodo]benzene in acetonitrile converted a range of (E)-3-butenoic acids into the corresponding butenolides in good yields.
One-pot synthesis of 5-Alkylfuran-2(5H)-ones
Ma, Jie,Wang, Si Hong,Guan, Rong Tian
, p. 1229 - 1233 (2007/10/03)
5-Alkylfuran-2(5H)-ones can be efficiently obtained using a one-pot approach, starting from methyl 3-nitropropanoate and aldehydes, in ethyl acetate, with Amberlyst A-21 as catalyst, in 60-90% overall yield. Copyright Taylor & Francis Group, LLC.
Regioselective Alkylation of 2-Trimethylsiloxyfuran; Direct Access to 4-Substituted But-2-en-4-olides
Jefford, Charles W.,Sledeski, Adam W.,Boukouvalas, John
, p. 364 - 365 (2007/10/02)
Primary iodides alkylate 2-trimethylsiloxyfuran in the presence of a molar excess of silver trifluoroacetate to give the 4-alkylbut-2-en-4-olides in 55-81percent yield; as an illustration of the method, the cytotoxic marine sponge constituent, 4-(methoxycarbonylmethyl)but-2-en-4-olide was prepared in 79percent yield in one step.
SYNTHESIS OF 5-ALKYL-3H-THIOLEN-2-ONES AND 5-ALKYL-3H-FURAN-2-ONES AND CONDENSATION REACTIONS AT THE HETEROCYCLIC METHYLENE GROUP
Sedavkina, V. A.,Morozova, N. A.,Egorova, A. Yu.,Ostroumov, I. G.
, p. 377 - 380 (2007/10/02)
The intramolecular cyclization of γ-ketocarboxylic acids and their esters gives 5-alkylsubstituted 3H-thiolen-2-ones and 3H-furan-2-ones.It was shown that reaction occured at the heterocyclic methylene group and that the conditions under which the reaction took place depended on the nature of the heterocyclic atom.
SYNTHESIS OF α,β-UNSATURATED BUTENOLIDES FROM ALLENIC ACIDS
Gill, G. Bryon,Idris, Muhammad Sum Hj.
, p. 4811 - 4814 (2007/10/02)
The electrophile-initiated cyclisation of allenic acids and esters provides a general route for the synthesis of β-substituted α,β-unsaturated butenolides.
